


seeing the pain, seeing the pleasure

by assholemurphamy



Series: Touch Me (I Wanna Be Dirty) [2]
Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Anal Sex, Angel Castiel, Blow Jobs, Bottom Sam, Butt Plugs, Cock Slut Sam, Dirty Talk, Dom Dean, Dom/sub Undertones, Fem!Castiel, Gender or Sex Swap, Incest, Loud Sex, M/M, Multiple Orgasms, Non-Consensual Voyeurism, Oral Sex, Plot What Plot/Porn Without Plot, Prompt Fill, Sex Swing, Sex Toys, Sibling Incest, Size Kink, Slut Sam, Spanking, Sub Sam, Top Dean, Voyeurism, cas is cassandra, castle sex, dean has a really dirty mouth, like a lot, mutual orgasms, needy sammy, pigtail sam, sam is a little sub, they dont know theyre being watched
Language: English
Status: Completed
Published: 2016-10-02
Updated: 2016-10-02
Packaged: 2018-08-19 05:26:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8191831
Author URL: https://archiveofourown.org/users/assholemurphamy/pseuds/assholemurphamy
Summary: While exploring an abandoned castle, the Winchesters's find a locked room.When they enter the room, they are surrounded by all kinds of kinky sex toys. From sex swings to breeding benches to floggers and whips, canes, gags and butt plugs.Dean jokes about how awkward it would be if one of them were to get hard right now.Turns out, Sam's one step ahead of him...~~~“Dean…” He starts, tipping his head slightly to the side. Allowing his brother to have better access. “Fuck…”The older boy just smirks and drags his tongue over his brother’s collarbone.“Okay.” Dean rests his hands on Sam’s waist, tucking one up underneath one of his ever-present plaid shirts. “We can do that.”





	

**Author's Note:**

  * For [LuciferDiggsLiasWorksSoYouShouldToo](https://archiveofourown.org/users/LuciferDiggsLiasWorksSoYouShouldToo/gifts).



> This is a prompt fill for a (v long) prompt that was left on part 1 of this series. 
> 
> I had a lot of fun writing this, and i honestly had to delete a bunch of stuff bc it didn't fit the plan i had written out. 
> 
> You should read pt.1 if you are interested in my take on FirstTime!wincest :D  
> But you don't have to read that one for it to make sense.
> 
> (Title is from Pillow Talk by Zayn)

{Context: The boys are hunting a king’s spirit, but it only comes out once a year. The pair gets to the abandoned site a few days early.  
While exploring the castle, the pair find a locked room. Thinking it could help solve the case, they search the house for the key, when they can't find it, Dean shoots the door handle. It opens.}

“Holy shit…” Dean breathes out, aiming the flashlight around the room, “Sam, how awkward would it be if one of us got hard right now.” 

Dean walks a little farther into the room, laughing at the thought.

“What’s the matter, Sammy?” Dean smirks when he sees him turn away. “Oh, are you already hard, little brother?” 

Dean licks his lips and walks to him, pressing the boy up against the nearest dresser, kissing slowly and seductively up his neck, humming softly against -what he knows, are- Sam’s soft spots.

“Dean…” Sam starts, tipping his head slightly to the side. Allowing his brother to have better access. “Fuck…”

The older boy just smirks and drags his tongue over his brother’s collarbone. “Okay.” Dean rests his hands on Sam’s waist, tucking one up underneath one of his ever-present plaid shirts. “We can do that.”

Sam looks down at his brother, confused for a moment before it clicks. His cheeks are tinted pink in the dimly-lit room and Dean can’t help but pull him down for a harsh kiss. Their lips meet harshly and Sam’s hands fall to his older brother’s ass, palming it softly in his wide hands. 

“Mmm, Sammy- no.” Sam rolls his eyes at Dean’s stupid ‘never-bottoming’ rule and moves his hands back up towards his lower back. The pair are well-aware of how loud they are being, but with nobody else in the house, they figure it's now or never. After all, having their father walk in on them in the motel room was awkward enough.

Across the castle, Cassandra wanders through the library, flicking through some old dusty manuals, and waiting for her friends to return. She would have considered calling them, if it weren't for the distinct sound that she heard next, it was the same sound Dean had made when they engaged in sexual activities together, her first month being human.

The angel, growing more d more concerned, trekked her way across the dusty castle, to find her friends. The sounds amplified as she made her way closer and closer to the open door. The moans seeming to bounce off of the walls and solid-granite floor.

Dean had informed her that there was nothing wrong with human sexuality, and it was nothing to be ashamed of, she she decided to watch. 

“Dean- there’s so-someone in here…” Sam stutters as his brother sucks a large purple hickey on his neck. 

“Kinky,” He mumbles, smirking against the purpled skin under his lips. 

Sam rolls his eyes and pulls away a little, looking around, not finding anyone. “Dean I’m serious. T-there's a girl in here…” 

“Sammy, is this some of that ‘no homo’ crap, because I was literally balls deep this morning. I don’t think that shit counts anymore.” Dean chuckles and presses his lips to Sam’s once more before pulling him gently towards the corner of the room. “Come sit in this swing, babe. Wanna see if we should get one for the bunker.”

Sam strips off his pants and sits in the sex swing, letting Dean tie his feet against the straps, giving him perfect access to his pretty hole. Dean picks up a bottle of lube from the dresser and smirks, wiping the dust off of it, onto his shirt. 

“You ready, little brother?” Dean doesn’t even wait for the inevitable yes before he is pouring the slick substance over the taller boy’s fluttering hole. “Good boy.”

Sam moans softly at the coldness, and Dean lowers his hand, spreading the liquid over his entrance, biting his lip gently. 

“D-Don’t touch my cock, D-Dean… Wanna cum just from y-yours…” Sammy mutters, and his brother lets out a groan, feeling his dick twitch in his pants. 

“Jesus Christ, bro.” The older man slicks up two fingers and presses it into the warm wet heat, enjoying the whines he receives as he does so. “Always ready to take my cock, aren't you baby?”

Sam nods vigorously and mumbles his conces to begin. Dean rucks down his pants, eagerly and lines up his cock, rubbing a lube covered hand over it quickly. 

“G-go, Dean please…” 

Dean smirks and presses into his little brother slowly, waiting for him to get comfortable before he begins thrusting. The older boy grips Sam’s thighs and starts slowly dragging his cock in and out of him, teasingly. 

Sam rolls his eyes and pulls Dean's lips down on his own, letting his brother suck and bite away as he pleases, tangling his hands in his short hair while his thrusts start to pick up speed. Dean licks over Sam’s lower lip once more before pulling away, focusing again on his thrusting. He snaps his hips forward and groans when he sees Sammy’s eyes roll into the back of his head in pleasure.

“Oh god, s-so good, Dean.”

“Yeah, you like it when your big brother fucks you?” Dean asks rhetorically, a smirk pulling at the corner of his lips. “Yeah you do, love it when my big thick cock is buried inside of you; makes you look like a total cockslut, baby boy. But that's alright, isn't it? Because that's what you are, huh? Love being a little toy for your big brothers amusement.”

Samis wreathing against his brother’s hold, moaning obscenely and trying to gain enough momentum from his position in the swing to fuck back against him.

From Cas’ place on the ceiling, she lays down on her stomach against one of the rafters, and starts grinding her pelvis against the smooth wood. She bites her lip to keep quiet, only letting out small breaths while she watches the scene play out before her. 

This wasn’t the first time she had scene them in the throws of ‘love-making’ as Dean had called it, but it was, however, the first time she was sticking around to watch. 

Dean leans over his brother and attaches their lips, pounding deep into his hole. He swallows Sam’s needy moans and shaky breaths before pulling away just enough to pick up the pace again. He can feel the thin layer of sweat coating his skin, and he reaches up to wipe his forehead with the back of his hand.

“D-Dean, harder! P-please fuck me, I’m gonna cum!” He shouts, clearly out of breath.

His brother complies and fucks into him harder, knowing he was close too. He reaches forward, bringing Sam’s wrists to his mouth and begins sucking a deep hickey, making him go crazy. Not a moment later, is Sam cumming hard against his chest, his hole clenching tightly around his brother’s thick cock. 

“Fu-fuc-fuck… Deeeean,” Sam whines, shivering slightly as the aftershocks of his orgasm ripple through him and his brother empties his load into him.  
Dean unties his brother from his position in the swing, and pulls out of him, making Sam whine. 

“Awe, baby, do you already miss having my cock inside of you?”

Sammy gives a weak nod, shuddering at the feeling of his brother’s cum leaking out of his hole. Dean smirks and grabs a buttplug from the top drawer of the dresser. He blows off the dust, rubbing the rest off with his shirt and walks to his brother, pressing it inside of him.

“There you go little slut, good to go, right?” Sam nods blissfully and bites his lip when he feels it graze his prostate gently. “Does it feel good, Sammy?” 

He nods and rocks back against it, rolling his hips gently, locking his eyes with Dean’s. 

“Moan for me, little baby.” He whispers to him, and Sam complies quickly, pressing his palm against his cock, moaning loudly. “Good boy. Show me what else that mouth can do.”

Sam blushes and hops off of the sex swing, sinking almost instantly to his knees in front of his brother. Dean holds his half hard cock in his hand, pressing it to Sam’s lips and he opens obediently, suckling on the tip, causing Dean to grip his hair, pressing him down farther. 

Dean knows Sam still cannot take his cock all the way in his mouth, but he still expects the boy to suck like a proper whore. 

Sam giggles against his length and sucks him down, half of the 10” cock fitting easily down his throat. He starts bobbing his head, sucking sloppily, dragging his tongue against the the large vein along the bottom. 

‘Lord, his hair is getting long’ Dean thinks when Sam tucks it behind his ear for the third time. ‘Oh!’ He reaches down to grip his brothers gorgeous hair, biting his lip when Sam halts his movements, in favour of resuming his suckling. Dean ties his hair up in a ponytail behind his head, using Cassandra’s hair band on his wrist.

“Mmm, you look so pretty Sammy. Could look so pretty all the time, if you lost the flannels sometimes, baby brother.” 

Sam glares at him and drags the edge of his teeth along his brothers cock, making him pull back slightly. Dean pulls out of sam's mouth and smirks at the string of spit connecting his cock to his brothers red puffy lips.

He leans down and says with a deep authoritative voice, “What was that for, sweetheart? Trying to get me to punish you?”

Sam doesn't say anything, just looks up at his brother with eyes blown wide with lust, rocking against the plug. 

“Answer me, sammy.”

“Y-yes, I would like to be punished.”

“Good girl. Climb up on the bench, would you?”

Sam climbs up onto the padded bench, lying on his stomach and Dean grabs a paddle, one with a heart shaped cut out. 

“I want you to count for me, gorgeous. I will give you 10 slaps.” Dean rubs a calloused hand over the boy’s ass. “Remember, you can always use the safe word if it gets to be too much, alright?”

Sam nods and takes a deep breath, bracing himself.

“One… Two...T-three,” He can feel himself getting hard again from the punishment and gasps from the fourth hit. “Fuck- F-four, Fiveee…”  
The next few come in quick concession, almost not giving him enough time to recover, “Six, Seven, Eight… N-nine… TEN!”

He shouts the last number as it was by far the hardest, and he knows his bum is probably bright red by now. 

“Thats better. Now, sit up properly.”

Sam sits up on the bench, as Dean lines his cock up with his lips again, and presses inside. He sucks like a good boy, and only gags twice. But that's okay, bc Dean knows how much his huge cock can hurt his boy’s throat. 

When Dean nears the edge, once again, he pulls his cock out of Sam’s mouth, holding it over his face as he jerks himself off, climaxing with a loud groan and cumming over his brothers pretty face. When Dean opens his eyes again, he almost feels himself getting hard once more, the cum had fallen against Sammy’s lips and he was licking it off, clearly enjoying himself. 

“Baby, would you like to cum again?” Dean asks, running a hand through his baby brothers hair, careful to avoid the ponytail. He looks down at his little boy and has to hold back a moan… Sam had cum just from sucking him off… 

‘What a good little brother,’ Dean thinks, leaning down to kiss his lips, tasting himself on the man’s lips.

“I liked t-that a lot, thank you Dean.” Sam tells him, from his position on the bench.

“Yeah, your welcome, baby.” Dean chuckles, walking to his clothes and beginning to get dressed again. “I say we loot this place and hide all this shit in baby… At least ‘til we get back to the bunker.”

“Really? Where will we even put all of it.” Sam laughs, standing himself and pulling his shirt on again, deciding to leave the buttplug in, for Dean’s sake.

“Well, we don't need 2 libraries, do we?”

Sam rolls his eyes and laughs, taking the ponytail out of his hair and flinging the elastic at his brother.

“Awe, are you guys done now?” Comes a voice, sounding slightly disappointed.

“Cas?!” They both say in unison, looking up at the ceiling, to find her on her back, watching them.

“Yeah, I didn't want to uh… interrupt…”

“Wait- were you…?!” Dean asks, putting it all together in his head, “CASSANDRA!”

She giggles and shrugs, hopping down easily and kissing each boy on the nose, like a child would.

“Looked like you two were having fun… And so did I.” She giggles once more, winking at Dean before skipping out of the room.

**Author's Note:**

> I really liked writing this, and part 3 might involve Impala!sex, so let me know in the comments if you would be interested in reading that.  
> As well as any other prompts/kinks you would be eager to read. :)
> 
> Be sure to leave kudos please!
> 
> You can come bug me on tumblr also, assholemurphamy.tumblr.com


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